Hi @Sibley Scarlett, ,
Is your event list like below?
As per my knowledge, overlay calendar views will not be displayed after connecting to Outlook. Indeed, only the event list is connected to Outlook and those you wanted items are in your absence request list. Since there is no item actually in event list, you are going to see nothing in outlook. You can verify this point by accessing work from home view page or vacation view page, you will find Connect to Outlook feature is disabled on those view pages. It is not supported for a list(except calendar/event list) to connect to Outlook.
The alternative way is to create a calendar/event list specifically to store the list items whose absence type == work from home and create a calendar/event list to store the list items whose absence type == vacation. Connect both two event lists to Outlook, check two calendars in Outlook, right-click one calendar and select Overlay.
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